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Both are mostly episodic anime about a main character who solves mysterie. The two main characters, Houtarou and Holmes, use logic to deduce simple mysteries. The main difference is that Hyouka takes place in a high school while Kyoto Teramachi Sanjou no Holmes takes place at an antique shop in Kyoto. Both shows have a relaxing atmosphere and a small romance subplot.

They both have some overarching plot, Tenma trying to confess to Karasuma and Sunako becoming a lady, while each episode is filled with some silly randomness that you can't help but enjoy.

Kakegurui has the same art style and the same ecchi outlook as Prison School. When you lose a game in Kakegurui, you become a housepet and are treated very similarily if you were stuck inside the Prison School. The sado-masochism part of Kakegurui is too much alike Prison School. Very good anime, so if you liked Prison School, give Kakegurui a shot.

The biggest similarity between No Game No Life and Kakegurui is the game aspect. In No Game No Life, you have to play a game to settle any argument. You don't have to play a game to settle everything in Kakegurui, however the characters choose to do it any way.